1. Field of the Invention
The invention relates to new 1-aryl-5-(substituted alkylideneimino)pyrazoles and to processes for their preparation. The invention further pertains to compositions of said compounds and methods, using said compounds, for the control of arthropod, nematode, helminth or protozoan pests. In particular it relates to the application of said compounds or compositions in agricultural methods of use, particularly as pesticides, for controlling arthropods, especially insects via ingestion or contact action.
2. Description of the Related Art
Various 1-(substituted phenyl or pyridyl)-5-(substituted amino) pyrazole compounds are known to exhibit a number of different types of pesticidal activity, including activity as herbicides, plant growth regulators, insecticides, and nematicides. Included among these are the following:
U.S. Pat. No. 4,863,937 discloses as insecticides, acaricides and nematicides 1-aryl-5-(substituted alkylideneimino)pyrazoles, which are unsubstituted or alkyl or haloalkyl substituted in the 3-position of the pyrazole ring;
EP 301,339 and corresponding CAS reference 111(5):39360c disclose 1-(substituted aryl)-5-(substituted aryl methylideneimino)pyrazole compounds-(per pages 3, 6, 10 and 16 of the reference) as intermediates to insecticidal compounds. The compounds are unsubstituted or alkyl or haloalkyl substituted in the 3-position of the pyrazole ring;
J. Prakt. Chem., 332(3), 351-8, 1990, Hennig L. et al., corresponding to CAS reference 113 (25):231264 g, is a chemistry article which discloses 1-phenyl-5-(substituted phenyl methylideneimino) pyrazole compounds, which are either methyl or phenyl substituted in the 3-position of the pyrazole ring. There appears to be no disclosed pesticidal activity;
GB 923,734 discloses 1-aryl-5-(substituted phenyl methylideneimino)pyrazole compounds as dyes and which are only substituted by cyano in the 3-position of the pyrazole ring;
U.S. Pat. No. 4,685,957 discloses 1-aryl-5-(substituted iminoamino)pyrazoles as herbicides and plant growth regulators, which compounds are unsubstituted or alkyl substituted in the 3-position of the pyrazole ring;
EP 295,117; WO 87/03781 (also corresponding to EP 234,119); EP 295, 118; and EP 350,311 disclose 1-phenyl-5-(substituted amino)pyrazole compounds for control of arthropod, nematode, helminth and protozoan pests;
GB 2,136,427 discloses as herbicides 1-(substituted-2-pyridyl)-5-(substituted amino)-4-cyanopyrazoles, which are unsubstituted at the 3-position of the pyrazole ring;
U.S. Pat. No. 4,772,312 discloses as herbicides 1-(substituted-2-pyridyl)-5-(substituted amino)pyrazoles, which are unsubstituted or alkyl substituted in the 3-position of the pyrazole ring;
U.S. Pat. No. 4,804,675 discloses as insecticides, acaricides, and nematicides 1-(substituted-2-pyridyl)-5-(substituted amino)pyrazoles, which are unsubstituted or alkyl or haloalkyl substituted in the 3-position of the pyrazole ring;
U.S. Pat. No. 4,740,232 discloses as herbicides 1 -(substituted phenyl)-5-(substituted amino)pyrazole compounds, which are unsubstituted in the 3-position of the pyrazole ring;
EP 398,499 discloses phenyl substituted heterocyclic compounds as insecticides and acaricides, including 1-(substituted phenyl)-5-(substituted amino)pyrazoles.
U.S. Pat. No. 4,822,810 discloses 1-aryl-4-cyano-3-(sulfur substituted)-5-(alkoxyalkylideneimino)pyrazoles for the control of arthropod pests.
U.S. Pat. No. 3,686,171 discloses N'-[(4-hydroxymethyl or formyl)-5-pyrazolyl]amidines as intermediates or anti-inflammatory agents.
U.S. Pat. No. 2,998,419 discloses the process of manufacture and use of affinity for proteins of 5-(substituted amino)-3,4-dicyanopyrazoles.
Acta Chimica Academiae Scientiarum Hungaricae, Tomus 105(2), 127-139 (1980), Simay, T. et al., discloses the chemical synthesis and physical properties of various 5-(substituted amino)pyrazoles (for examples compounds 2, 4, 7, 8 and 15-18).
It is thus apparent that the nature and position of substituent groups on a pyrazole ring provide widely different types of biological activity which type and level of activity is not readily apparent.